Top Tech Jobs & Startup Jobs in Toronto

Serve as a client-facing compensation advisor partnering with HR and business leaders to design and implement compensation programs, conduct market benchmarking and analytics, support pay decisions, drive global compensation processes, deliver training, and collaborate with Recruiting on offers and pay equity.

Own and architect the enterprise context layer for AI: set strategy, standards, and operating model for knowledge, metadata, provenance, and permissions; design control models for AI actions; drive platform/connector strategy; build federated stewardship and lifecycle policies; measure retrieval and grounding quality and partner with Legal, Privacy, Security, IT, and Engineering.

Lead strategic, high-visibility design initiatives for Dropbox Bridge AI efforts. Define opportunities, own projects from concept to delivery, simplify complex workflows, prototype with generative AI, and ensure high craftsmanship. Influence product and design strategy, collaborate cross-functionally with product and engineering, mentor designers, and elevate design quality and storytelling across distributed teams.

Lead Dropbox's enterprise competitive intelligence across multiple product lines. Build an operating model to collect, analyze, and distribute competitive and market insights. Produce executive briefings, battlecards, win/loss analysis, and actionable recommendations to inform sales, product, and GTM strategy. Modernize programs using AI, automation, and research platforms while partnering cross-functionally to measure impact and enable customer-facing teams.

Own and operate the Workforce Planning operating system: plan and run governance forums and reporting, track milestones/dependencies/risks, enable adoption of tools and outputs, package and distribute insights, coordinate cross-functional delivery, build templates/playbooks, run training, and prepare executive materials to ensure consistent, scaled workforce planning operations.

Lead cross-organizational technical strategy and execution for core sharing and collaboration systems. Architect and implement foundational frontend/backend and platform solutions at massive scale, drive AI/LLM adoption, mentor engineering leaders, resolve systemic bottlenecks, and remain hands-on in critical design, prototyping, and code contributions.

Build and run Product Marketing operating systems to improve planning, portfolio visibility, messaging lifecycle, launch governance, and cross-functional accountability. Create templates, roadmaps, readiness criteria, and automation-enabled workflows; partner across functions to codify roles, decision rights, and handoffs; measure adoption and continuously improve processes to enable clearer, more consistent go-to-market execution.

Lead vision, strategy, and execution for Dropbox's next-generation design system and design technology platform. Build reusable patterns, components, tokens, and governance; partner with product, engineering, research, and brand; raise interaction, accessibility, and implementation quality; create adoption and measurement models; and develop a multidisciplinary team to scale coherent, high-quality multi-product experiences including AI-native capabilities.

Lead global sales compensation, quota strategy, and incentive planning. Design governance, drive quota and payout execution, partner with Sales, Finance, HR, and Systems, own incentive platform operations, and build a high-performing compensation team to support SaaS revenue objectives.

The Head of Scaled Sales will build sales-assisted growth strategies, optimize customer engagement, leverage data analytics, and deploy AI in sales processes.